Enantioselective catalytic alpha-alkylation of aldehydes via an SN1 pathway

J Am Chem Soc. 2010 Jul 14;132(27):9286-8. doi: 10.1021/ja103618r.

Abstract

Primary aminothiourea derivatives are shown to catalyze enantioselective alkylation of alpha-arylpriopionaldehdyes with diarylbromomethane. Evidence for a stepwise, S(N)1 mechanism in the substitution reaction induced by anion binding to the catalyst is provided by catalyst structure-activity studies, kinetic isotope effects, linear free-energy relationship studies, and competition experiments.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Aldehydes / chemistry*
  • Alkylation
  • Catalysis
  • Hydrocarbons, Brominated
  • Organic Chemistry Phenomena
  • Stereoisomerism

Substances

  • Aldehydes
  • Hydrocarbons, Brominated
  • methyl bromide